The Great First-Date Prenup Experiment

After casually dating a man for a month, my friend Holly was ready to cease interaction. They hadn’t communicated in a week, which she thought signalled a “fadeaway” breakup. But then he texted: “Hey hey.”

“First, kill anyone who says ‘hey hey,’” I instructed, bristling at the casual pose. (Other lethal word repetitions include “cool cool” and “swag swag.”) “So after we put out a fatwa on ‘hey hey,’ should I reply? Ignore?” Holly asked. “I just want to end this in the way he finds most socially acceptable. Because though I don’t feel like I owe him anything, given the option, I would rather be nice.” Breakup etiquette and basic karmic decency require the dumper to cater to the dumpee. But the best way to get dumped is a polarizing matter: Whereas some prefer the dignity (and plausible deniability) of a slow fade, others find silence rude, clinging to hope and falling into self-doubting spirals as they wait for one last reply. “The problem is I don’t know what ‘nice’ means to him,” Holly lamented.

There is a wealth of literature devoted to “pickup lines” and “pickup artistry.” Fewer resources are dedicated to the art of ending it. But to date actively is to be in a state of perpetual breakups. For all the pressure placed on choosing and wooing potential partners, ruling someone out is at least as important as deciding to consider him in the first place. In a monogamous society, the worst possible scorecard for breakups is the total number of people you ever dated; the best is that number, minus one.

“It should be a rule that at the beginning of every dating interaction, you must declare whether you prefer a clear or faded breakup,” I said to Holly. “A dating prenup, established before the first date.” We ran down the list of polarizing breakup negotiations: Who gets custody of shared friends? Are you among the 35 percent of people who find ex sex therapeutic, or will it cause irreparable harm? Can I stay friends with your friends’ girlfriends? Do you like to stay friends with your exes, or should I plan on never seeing you again if the sexual chemistry sucks? Ironclad nudie-pic deletion policy is a must, if sexters are ever to rest safely. The return of gifts is negotiable; a gift of value given within two weeks of the breakup should be returned unless specifically advised otherwise. I will cave to any demand that buys me the right to keep the oversize shirts I have absorbed into my wardrobe. Perhaps we could negotiate a clause establishing a ticking-clock system of fixed rewards? For every six months we stay together, I may keep one oversize sweater, or two T-shirts. Will have ex sex in exchange for broken-in jeans.

“One of us needs to try this on a man in the wild,” Holly concluded. As luck would have it, I had a first date planned for that night.

He was surprisingly open to the concept, mostly because prior to the moment I said “first date,” he was among the 69 percent of single Americansunsure whether a particular outing counts as a “date.” Now that he knew there was a possibility of getting laid, he was willing to answer any questions. He prefers enunciated breakups. He sometimes stays friends with exes, but does not require it. I announce that I don’t do ex sex (unless jeans are on the table) and that “hey hey” is grounds for dumping.

While we negotiated the terms of our dating prenup via Facebook message, I opened another browser tab and GChatted my friend Anne. When I told her what I was doing, she reacted with horror. “This is a thing people are doing?! If someone gave me a dating prenup, I wouldn’t go on a date with him. My dating prenup is that you can’t give me a prenup.” Establishing rules is a buzzkill, she reasoned, not to mention the implied doom of planning broken hearts.

Romance requires optimism, and casual dating sometimes requires a suspension of disbelief. Though the odds that any one date turns into a sweeping love story or the best sex of your life are low, the only guarantee that it won’t is ruling out the possibility too soon. We enter first dates in a state of hope. Would talking about the (likely) possibility of failure destroy hope, though? Or could it be an expression of utopian relationship ideals, a mechanism for improving social rituals and communication? The only way to find out was to interrogate my prenup guinea pig for post-date analysis. If he’s too cowardly to talk about his feelings, I reasoned, he’s not worth dating anyway. (Because he’s probably boring.)

“It was sort of intimidating to be reminded the date could go poorly, and you might want to get rid of me,” my date reflected. “I did feel more like I had to impress you, but it wasn’t bad. More like, ‘let’s do this.’” Though Anne’s buzzkill theory had been convincing, the date went well. Having already opened a discussion on personal dating philosophies, however, we found ourselves having two parallel conversations all night: One was a regular first-date getting-to-know-you talk, and the other was a running commentary on how the date was going. We were on a director’s cut date. “This was a great date,” he announced at the end, before candidly discussing traits most likely to torpedo a theoretical relationship between us. “I guess the only way to find out is to do it,” he concluded.